Reaction of thioacetals with triethylsilane in the presence of Lewis acids and reduced nickel
1,1-Di(alkylthio)alkanes, 1,3-oxathiolanes, 1,3-dithiolanes, and ortho thioesters are cleaved by triethylsilane in the presence of catalytic amounts of zinc iodide or reduced nickel. In the presence of zinc iodide the acyclic dithioacetals and ortho thioester are converted into alkyl sulfides and triethyl(alkylthio)silanes by cleavage of the carbon-sulfur bond. The analogs of the cyclic acetals are cleaved by triethylsilane only in the presence of reduced nickel, while regio-specific cleavage of the heterocycle at the carbon-oxygen bond is observed in 1,3-oxathiolanes. The cleavage of the 1,3-dithiolanes takes place by a more complicated mechanism with the formation of the disilyl ether of ethanedithiol, hexaethyldisilylthiane, and triethyl(alkylthio)silanes. The cyclic ortho thioester reacts with triethylsilane both at zinc iodide and at reduced nickel with the formation of the products from preferential cleavage of the exocyclic bond.
- Research Organization:
- Ufa Petroleum Institute (USSR)
- OSTI ID:
- 5887271
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:9; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ACETALS
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL BONDS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHROMATOGRAPHY
DISSOCIATION
ELEMENTS
ETHERS
HALIDES
HALOGEN COMPOUNDS
HYDRIDES
HYDROGEN COMPOUNDS
INORGANIC ACIDS
IODIDES
IODINE COMPOUNDS
KINETICS
LEWIS ACIDS
METALS
NICKEL
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SILICON COMPOUNDS
ORGANIC SULFUR COMPOUNDS
REACTION KINETICS
SEPARATION PROCESSES
SILANES
SILICON COMPOUNDS
SPECTRA
TRANSITION ELEMENTS
YIELDS
ZINC COMPOUNDS
ZINC HALIDES
ZINC IODIDES